Ibipinabant

Ibipinabant
Systematic (IUPAC) name
	4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	464213-10-3
ATC code	None
PubChem	CID 9826744
UNII	O5CSC6WH1T
KEGG	D09349
ChEMBL	CHEMBL158784
Chemical data
Formula	C24H22Cl2N4O2S
Mol. mass	501.427
	SMILES c2cc(Cl)ccc2C1=NN(C(NC)=NCS(=O)(=O)c3ccc(Cl)cc3)CC1c4ccccc4;
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Ibipinabant (SLV319, BMS-646,256) is a drug used in scientific research which acts as a potent and highly selective CB₁ antagonist.^[1] It has potent anorectic effects in animals,^[2] and was researched for the treatment of obesity, although CB₁ antagonists as a class have now fallen out of favour as potential anorectics following the problems seen with rimonabant, and so ibipinabant is now only used for laboratory research, especially structure-activity relationship studies into novel CB₁ antagonists.^[3]^[4]^[5]

References [edit]

^ Lange, JH; Coolen, HK; Van Stuivenberg, HH; Dijksman, JA; Herremans, AH; Ronken, E; Keizer, HG; Tipker, K et al. (2004). "Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists". Journal of Medical Chemistry 47 (3): 627–43. doi:10.1021/jm031019q. PMID 14736243. |displayauthors= suggested (help)
^ Need, AB; Davis, RJ; Alexander-Chacko, JT; Eastwood, B; Chernet, E; Phebus, LA; Sindelar, DK; Nomikos, GG (2006). "The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats". Psychopharmacology 184 (1): 26–35. doi:10.1007/s00213-005-0234-x. PMID 16328376.
^ Lange, JH; Van Stuivenberg, HH; Veerman, W; Wals, HC; Stork, B; Coolen, HK; McCreary, AC; Adolfs, TJ et al. (2005). "Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity". Bioorganic & Medicinal Chemistry Letters 15 (21): 4794–8. doi:10.1016/j.bmcl.2005.07.054. PMID 16140010. |displayauthors= suggested (help)
^ Srivastava, BK; Joharapurkar, A; Raval, S; Patel, JZ; Soni, R; Raval, P; Gite, A; Goswami, A et al. (2007). "Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: synthesis, biological evaluation, and molecular modeling in the homology model". Journal of Medical Chemistry 50 (24): 5951–66. doi:10.1021/jm061490u. PMID 17979261. |displayauthors= suggested (help)
^ Srivastava, BK; Soni, R; Joharapurkar, A; Sairam, KV; Patel, JZ; Goswami, A; Shedage, SA; Kar, SS et al. (2008). "Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-(4-chlorophenyl)-sulfonyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole". Bioorganic & Medicinal Chemistry Letters 18 (3): 963–8. doi:10.1016/j.bmcl.2007.12.036. PMID 18207393. |displayauthors= suggested (help)

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[1] Lange, JH; Coolen, HK; Van Stuivenberg, HH; Dijksman, JA; Herremans, AH; Ronken, E; Keizer, HG; Tipker, K et al. (2004). "Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists". Journal of Medical Chemistry 47 (3): 627–43. doi:10.1021/jm031019q. PMID 14736243. |displayauthors= suggested (help)

[2] Need, AB; Davis, RJ; Alexander-Chacko, JT; Eastwood, B; Chernet, E; Phebus, LA; Sindelar, DK; Nomikos, GG (2006). "The relationship of in vivo central CB1 receptor occupancy to changes in cortical monoamine release and feeding elicited by CB1 receptor antagonists in rats". Psychopharmacology 184 (1): 26–35. doi:10.1007/s00213-005-0234-x. PMID 16328376.

[3] Lange, JH; Van Stuivenberg, HH; Veerman, W; Wals, HC; Stork, B; Coolen, HK; McCreary, AC; Adolfs, TJ et al. (2005). "Novel 3,4-diarylpyrazolines as potent cannabinoid CB1 receptor antagonists with lower lipophilicity". Bioorganic & Medicinal Chemistry Letters 15 (21): 4794–8. doi:10.1016/j.bmcl.2005.07.054. PMID 16140010. |displayauthors= suggested (help)

[4] Srivastava, BK; Joharapurkar, A; Raval, S; Patel, JZ; Soni, R; Raval, P; Gite, A; Goswami, A et al. (2007). "Diaryl dihydropyrazole-3-carboxamides with significant in vivo antiobesity activity related to CB1 receptor antagonism: synthesis, biological evaluation, and molecular modeling in the homology model". Journal of Medical Chemistry 50 (24): 5951–66. doi:10.1021/jm061490u. PMID 17979261. |displayauthors= suggested (help)

[5] Srivastava, BK; Soni, R; Joharapurkar, A; Sairam, KV; Patel, JZ; Goswami, A; Shedage, SA; Kar, SS et al. (2008). "Bioisosteric replacement of dihydropyrazole of 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-(4-chlorophenyl)-sulfonyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole". Bioorganic & Medicinal Chemistry Letters 18 (3): 963–8. doi:10.1016/j.bmcl.2007.12.036. PMID 18207393. |displayauthors= suggested (help)

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Ibipinabant

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